Azo-dyes derived from naphthyl-aryl ethers



Patented Aug. 16, 1932 1 omen STATES.

' Lsnsiz P TEN gFFica ERNEST nenn'rnnn, or MID AND; MICHIGAN, Assrenon tonne now onmvrrclxr.

used.

; No Drawing.

- COMPANY, onmrnrnnnmrcnrennn oonronnrrouonivrroirreau- AZ OQDYES nnnrvnn rnom Application filed June 21,

*coNHRoR" where R, R and R represent naphthyl, aryl and diazotized amino-compound residues. respectively, such residues being capable of further substitution. 7 V It is known that azo dyes fast to light and Washing are'produced by coupling. diazotized aromatic amines into naphthol AS, the

latter being2.3-hydroxynaphthoic acid ani-v lide, or into related compounds. I have now discovered that aminonaphthyl-aryl ethers e. g. l-aminoA-phenOXy-naphthalene,. may be employed as arylide components, and fur: thermore that into arylides derived from such others and 2.3-hydroxynaphthoic acid by condensation or other suitable. manner, maybe coupled diazotized or polyazotized aromatic amino} or polyamino-compounds respectively, with the formation of useful azo-dyestufis. Theinvention, then, consists of the steps and new products hereinafter fully described and particularly pointed out in the claims, the following description setting forth but several of the various ways in which the principle of the invention may be NArHTHYL-ARYL nannies l.

1929. Serial mxerasoe.

Theherein. describednew azo dyestufis if dye cotton and "other fibers directly in a wide range of colors, varying from orange to purple in clear and brilliant tones. While they;

are best applied by developing on the fiber, they may also be produced in any'of the ordinary ways e. g., prepared in. substance or deposited upon suitable substrata to form lakes, in which. forms they are useful pig- .ments on account of'their insolubility, stability and fastness. In other words, the respective reaction components may be brought together directly,- with or'without the aid of a diluting or solvent'medium, the dye being separated from the reaction mixture by any suitable means. Auxiliary"treatment, 'e. g.

, mordanting or after-treatment with metallic salts such as chromium, aluminum or copper salts for fixing the dye or' modifying its color tone, may be employed if desired in conjunction with the dyeing operation.

A preferred manner in-which the invention may be carried out is illustrated in the following specific examples; it being understood, however, thatsuch examples are not to be construed as a limitation upon the invention.

l lwamz olel V The 2.3hydroxynaphthoio acid arylide 0f l-aminoA phenoxy-naphthalene is prepared by condensing said acid amine with the aid of phosphorus'tric'hlo'ride' in thepresence of toluene in the usual manner whereby the'desired arylide forms as a solidphase intermixed with the liquid medium. The

purified arylide has a melting point of 175? C.- 5.1 1 V j 1 Cotton yarn is impregnated withfa-slightly alkaline solution of the abovevarylide to which may be addedadvantageously,but not necessarily, formaldehyde and em fixative, e. g. Turkey red oil oran aluminum-salt.

Said yarn is then immersed in adiazo solution r d f m pm n e ee lide..l; i is ye develops on the fiber and has a violet red color, the probable formula being:

' N-O-NHooorn ii In the aforementioned examples, cotton was the particular fiber used, however, other natural or artificial fibers, e. g. silk'or rayon may be employed without departing from the I I scope of this invention which is intended to I embrace not only the herein described dye- I stuffs but materials dyed therewith. v C Furthermore, dyestufi components other I than those particularly above ment oned may I be used i. e. other-diazoti'zed or olyazotized 75 c 2 V P a i r aromat c mono I or polyamlno -compounds i I Ewampzeg maybeutilized as diazo'components for the In a manner similar to that described in purpose'of couph'ng into the herein described Examplell, tetrazotized, dianis'idine isl'coue aryl1de -,-1 a dersto dg at he l tQI JlQi so pled into thesame arylide, theidyestn'ff devels 'dl'ates here n; mentioned may furthermore be. oping on the fiber, being of a blue color and either monoor poly-substituted, e. g. by having the probable formula-2 3 alkyl, halogen and/ornitro groups.

I I I I 7.

Ton 2i -o-onH-8o- 90 J Ewample 3 V i In'short, my invention in its broader-as 39 5 e'ct s 'sco es' com ounds of the herein de- Similarly, *as abovedescr bed, dlazot zed p d p d o d f h psnitro-benzene azotoluidineiscoupled'into 5 a 3 m gr em j the, aforemntionedgafylideII, The dyestufi' droxynaphthoic acid and am nonaphthyl: which develops on;theIfibIerIigIreddishviolet'in aryl ethers by any suitable manner, and azon'dihas e .pro ablefor ula dyes Clerlved therefrom. I I I I100 3 I Other modes of applyin the principle of i 7 (1H, 7 a D I I I I I I I my invention may be employed lnstead of c O QO the one explained, change being made as re- I I I I II II gards the materials emirloyedfprovided the I I ingredients stated by any of'the following on I Y claims or the equivalent of; such stated-,i'n-

, O II gredients beemployed. v I r I therefore particularly point out anddise tinctly claim as my invention 5 I I '1. In a process for the manufacture of new 110 Byv similar procedure I have; prepared azo-dyes, the step which consists in coupling other azo dyes as illustrated in the following a 2.8.-hydroXynap hthoyl amino naphthyltable, wherein the first column indicates the phenyl ether having the probable general amine of which the diazotized or polyazoformula, f I v. r

ti'zedfform was coupledinto the above menr 1 15 tioned arylid'e, and the second column the ap' proximate colorofthe produced dye.

- T ble 1 g, Color Md'yesm'lfi with a diazotizedar'omatic amino compound.

' 2. In a process for the'manufacture ofn'ew .ni 'm i ig 'j R dist m azo-dyes, the step which consists in coupling ti'fitiit'fifitiilitfilfiilflfffiii:11:: 111:: iifi giitfiea yd p yn pht y -l op en xr gl dttitoai'ltlfii3:31;: 3:133:11: D nger. formula I i I o-nitrnphannfidine Vlolet i I r I'I V 4-4'-diamino-dipheuylether I Carmine rose I v I 1 I hnnvidine Y Reddish violet V I l p -chlornmlnpna Rose red I I I @OH z-nithoxy-s-z'iminodiphenyl Vlolet red I I pphenetolernzo-alphamaphthylamine Y I Grayblue v I CQNH'- I 0 I I" "m-nit:oheuzene azo naphthylaxnxne II Gray blue I, I 0 II Tao with a diazotized aromatic amino compound.

3. Azo-dyes having probably the general formula,

x OONH/ n m wherein X represents the residue from a diazotized aromatic amino compound, and n is the number of diazo groups in the diazo component X.

4:. Azo-dyes having probably the general formula,

--0 ONE 0-0 x wherein X represents'the residue from a diazotized aromatic amino compound, and n is the number of diazo groups in the diazo component X.

5. Azo dyes having probably the general formula wherein R represents an aryl residue.

6. A20 dyes having probably the general formula wherein X represents an aryl residue. Signed by me this 18 day of June, 1929.

ERNEST F. GRETHER. 

